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Key Documents

A8001

Sigma-Aldrich

Aconitine

≥95% (HPLC), crystalline

Synonym(s):

Acetylbenzoylaconine

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About This Item

Empirical Formula (Hill Notation):
C34H47NO11
CAS Number:
Molecular Weight:
645.74
Beilstein/REAXYS Number:
74608
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

form

crystalline

color

white

solubility

H2O: 0.3 mg/mL
ethanol: 35 mg/mL

SMILES string

CCN1C[C@]2(COC)[C@H](O)C[C@@H](OC)C34C5C[C@]6(O)[C@@H](OC)[C@H](O)[C@@](OC(C)=O)(C5[C@H]6OC(=O)c7ccccc7)C([C@H](OC)C23)C14

InChI

1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21-,22-,23+,24+,25?,26?,27+,28-,29+,31+,32-,33?,34-/m1/s1

InChI key

XFSBVAOIAHNAPC-VBUFWTEXSA-N

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Application

Aconitine has been used:
  • to study its cardiotoxic effects along the pericardium meridian (PM) on cardiac rhythm in rabbits
  • as a standard in high-performance thin layer chromatography (HPTLC) fingerprinting method
  • in the aconitine-based lipo-alkaloids semi-synthesis

Aconitine is a neurotoxin which activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization and blocking the release of neurotransmitters. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection.

Biochem/physiol Actions

Aconitine is a diesterditerpene alkaloid found abundantly in the plant Aconitum genera. It possesses analgesic, antipyretic and antirheumatic activity. Aconitine is involved in blocking neurotransmission. It acts as a neurotoxin as well as a cardiotoxin. Aconitine triggers ventricular tachycardia (VT) and ventricular fibrillation (VF). It interacts with voltage-dependent Na+ channels which results in the depolarization of membranes. Aconitine may exhibit therapeutic effects against systemic lupus erythematosus (SLE). It also inhibits the reuptake of norepinephrine.
Neurotoxin. Activates tetrodotoxin-sensitive Na+ channels, inducing presynaptic depolarization, thus blocking the nerve action potential which, in turn, blocks the release of neurotransmitters and decreases the end plate potential at the neuromuscular junction. Aconitine also blocks norepinephrine reuptake. In the heart, aconitine induces ventricular tachycardia after intracoronary injection. In cultured ventricular myocytes, aconitine increases the duration of the action potential and induces the appearance of early after depolarization.

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Skull and crossbones

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Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Inhalation

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Customers Also Viewed

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1 of 2

Hongbin Zhu et al.
Talanta, 103, 56-65 (2012-12-04)
A fingerprinting approach was developed by means of UPLC-ESI/MS(n) (ultra-performance liquid chromatography-electrospray ionization/mass spectrometry) for the quality control of processed Radix Aconiti, a widely used toxic traditional herbal medicine. The present fingerprinting approach was based on the two processing methods
T Sawanobori et al.
Japanese heart journal, 37(5), 709-718 (1996-09-01)
The effects of antiarrhythmic agents, including Classes I and IV and 3-10 mM Mg2+ on aconitine-induced arrhythmias were examined using a conventional microelectrode and patch clamp method in Langendorff-perfused rabbit hearts and isolated guinea-pig ventricular myocytes. Intracoronary application of 0.1
Hong-Fei Zhang et al.
Analytica chimica acta, 724, 54-60 (2012-04-10)
A magnetic carbon nanomaterial for Fe(3)O(4) enclosure hydroxylated multi-walled carbon nanotubes (Fe(3)O(4)-EC-MWCNTs-OH) was prepared by the aggregating effect of Fe(3)O(4) nanoparticle on MWCNTs-OH, and combined with high-performance liquid chromatography (HPLC)/diode array detection (DAD) to determine the aconitines (aconitine, hypaconitine and
Hongbin Zhu et al.
Analytica chimica acta, 752, 69-77 (2012-10-30)
This study presents a novel and rapid method to identify chemical markers for the quality control of Radix Aconiti Preparata, a world widely used traditional herbal medicine. In the method, the samples with a fast extraction procedure were analyzed using
T Y Chan et al.
Veterinary and human toxicology, 36(5), 452-455 (1994-10-01)
Both "chuanwu", the main root of Aconitum carmichaeli, and "caowu", the root of A kusnezoffii, are believed to possess anti-inflammatory, analgesic and cardiotonic effects and have been used in Chinese materia medica mainly for the treatment of musculoskeletal disorders. They

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